Acid wool dyestuffs of the anthraquinone series



Patented Jan. 12, 1937 iJNlTED STATES PATENT OFFIQE ACID WOOL DYESTUFFS OF THE ANTHRA- QUINONE SERIES No Drawing. Application August 30, 1935, Serial No. 38,662. In Germany September 14, 1934 Claims.

The present invention relates to new acid wool dyestuffs of the anthraquinone series.

In accordance with our present invention new acid wool-dyestuffs of the anthraquinone series 5 are obtained by causing aliphatic, hydroaromatic or aromatic amines to react upon 1-amino-4- haiogenantliraquinone-Zsulfonic acids which have a sulfonamide group in a s-position of the other nucleus. Mixed aliphatic-aromatic amines 0 of the type of benzylamine are intended to fall within the scope of the term aliphatic amine. Our new dyestuffs are manufactured in the usual manner, for instance, by working in an aqueous alkaline medium while using copper salts as catalysts.

The new dyestufis which are obtainable in accordance with our present invention may be represented by the following formula:

0 NH2 lg I Y- s0.n

r- O/ i I IHX wherein X stands for an aliphatic, hydroaromatic or aromatic residue, one Y stands for a sulfonamide groupand the other Y stands for hydrogen. It is, to be understood that the hydrogen atoms of the sulfonamide group may be substituted by alkyl-, arylor hydroaryl groups, lower alkyl groups being preferably employed. These new dyestuffs are dissolved in Water with a vivid blue to bluish-green coloration and dye wool from an acid bath blue to bluish-green shades of excellent fastness to light. The dyestuffs show particularly good equalizing properties.

The following examples illustrate the invention Without restricting it thereto the parts being by weight:-

Example 1 10 parts of the sodium salt of l-aminoibromo-6-sulfodiethylarnidoanthraquinone 2 sulv is soluble in water with a vivid blue shade and dyes wool from an acid bath clear blue shades.

Example 2 Ewample 3 10 parts of l-amino-l-bromo-S-(dimethyl)- sulfonamidoanthraquinone-2-sulfonic acid are boiled for two hours with 30 parts of hexahydro- 2O aniline in the presence of 450 parts of water and 50 parts of alcohol with the addition of 6 parts of sodium carbonate and 0.5 part of copper sulfate. The alcohol and the excessof hexahydroaniline are removed from the reaction mixture 25 by blowing in steam. From the remaining solution the dyestufi is salted out by the addition of sodium chloride. It forms blue needles, which are soluble in water with a clear greenish-blue coloration and dye wool from an acid bath green- 30 ish-blue shades of excellent fastness properties.

Example 4 We claim: 45 1. The products of the formula fi NH: 0 Y S 03H (l r'urx wherein X stands for an organic radical selected 55 from the group consisting of aliphatic, hydlroarowherein X stands for an aromatic radical and I matic and aromatic radicals, one Y stands for an each Z stands for a lower alkyl group.

alkyl sulfonamide group and the other Y stands 4, h product of th formula for hydrogen. o NH, 2. The products of the formula H 5 0 NH: /C\ s our ll mo s 01H No,s H, E; H c I It I I N-OzS 0 H111 H: 10

0 v z u H I O NHX H: H: wherein X stands for an organic radical selected. 5' The product f the f rmula 7 1:: from the group consisting of aliphatic, hydroaro- O NH matic and aromatic radicals and. each Z stands 9} for an alkyl group. l\ o H 3. The products of the formula H30 0 NH: N-01sg I O 20 H i Z sonar 0 HNONHCOCH| NO:S 0 KLAUS WEINAND.

l, Q CURT BAMBERGER. 

